Chemistry:List of corticosteroids
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Steroid ring system.
This is a list of corticosteroids (glucocorticoids and mineralocorticoids) or derivatives of cortisol (hydrocortisone). Most esters of these corticosteroids are not included in this list; for esters, see here instead.
The most common structural modifications in synthetic corticosteroids include 1(2)-dehydrogenation, 6α-, 9α-, 16α-, and 16β-substitution (with a halogen or methyl group), 16α,17α-acetonidation, and 17α- and 21-esterification.
Natural
- 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) = 21-hydroxypregn-4-ene-3,11,20-trione
- 11-Deoxycorticosterone (deoxycortone, desoxycortone; 21-hydroxyprogesterone) = 21-hydroxypregn-4-ene-3,20-dione
- 11-Deoxycortisol (cortodoxone, cortexolone) = 17α,21-dihydroxypregn-4-ene-3,20-dione
- 11-Ketoprogesterone (11-oxoprogesterone; Ketogestin) = pregn-4-ene-3,11,20-trione
- 11β-Hydroxypregnenolone = 3β,11β-dihydroxypregn-5-en-20-one [1]
- 11β-Hydroxyprogesterone (21-deoxycorticosterone) = 11β-hydroxypregn-4-ene-3,20-dione
- 11β,17α,21-Trihydroxypregnenolone = 3β,11β,17α,21-tetrahydroxypregn-5-en-20-one [2]
- 17α,21-Dihydroxypregnenolone = 3β,17α,21-trihydroxypregn-5-en-20-one [3]
- 17α-Hydroxypregnenolone = 3β,17α-dihydroxypregn-5-en-20-one
- 17α-Hydroxyprogesterone = 17α-hydroxypregn-4-ene-3,11,20-trione
- 18-Hydroxy-11-deoxycorticosterone = 18,21-dihydroxypregn-4-ene-3,20-dione [4]
- 18-Hydroxycorticosterone = 11β,18,21-trihydroxypregn-4-ene-3,20-dione
- 18-Hydroxyprogesterone = 18-hydroxypregn-4-ene-3,20-dione [5]
- 21-Deoxycortisol = 11β,17α-dihydroxypregn-4-ene-3,20-dione,
- 21-Deoxycortisone = 17α-hydroxypregn-4-ene-3,11,20-trione
- 21-Hydroxypregnenolone (prebediolone) = 3β,21-dihydroxypregn-5-en-20-one
- Aldosterone = 11β,21-dihydroxypregn-4-ene-3,18,20-trione
- Corticosterone (17-deoxycortisol) = 11β,21-dihydroxypregn-4-ene-3,20-dione
- Cortisol (hydrocortisone) = 11β,17α,21-trihydroxypregn-4-ene-3,20-dione
- Cortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trione
- Pregnenolone = pregn-5-en-3β-ol-20-one
- Progesterone = pregn-4-ene-3,20-dione
The glucocorticoid activity of progesterone and 17α-hydroxyprogesterone is very weak (>100-fold less than that of cortisol).[1]
The above list includes precursors and intermediates in corticosteroid biosynthesis.
Synthetic
Progesterone-type
- Flugestone (flurogestone) = 9α-fluoro-11β,17α-dihydroxypregn-4-ene-3,20-dione
- Fluorometholone = 6α-methyl-9α-fluoro-11β,17α-dihydroxypregna-1,4-diene-3,20-dione
- Medrysone (hydroxymethylprogesterone) = 6α-methyl-11β-hydroxypregn-4-ene-3,20-dione
- Prebediolone acetate (21-acetoxypregnenolone) = 3β,21-dihydroxypregn-5-en-20-one 21-acetate
In addition to the above, various progesterone derivative progestins such as chlormadinone acetate, cyproterone acetate, medrogestone, medroxyprogesterone acetate, megestrol acetate, and segesterone acetate possess weak glucocorticoid activity which can manifest clinically at high dosages.
Hydrocortisone-type
- Chloroprednisone = 6α-chloro-17α,21-dihydroxypregna-1,4-diene-3,11,20-trione
- Cloprednol = 6-chloro-11β,17α,21-trihydroxypregna-1,4,6-triene-3,20-dione
- Difluprednate = 6α,9α-difluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-butyrate 21-acetate
- Fludrocortisone = 9α-fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione
- Fluocinolone = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione
- Fluperolone = 9α-fluoro-11β,17α,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dione
- Fluprednisolone = 6α-fluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
- Loteprednol = 11β,17α,dihydroxy-21-oxa-21-chloromethylpregna-1,4-diene-3,20-dione
- Methylprednisolone = 6α-methyl-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
- Prednicarbate = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-ethylcarbonate 21-propionate
- Prednisolone = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
- Prednisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione
- Tixocortol = 11β,17α-dihydroxy-21-sulfanylpregn-4-ene-3,20-dione
- Triamcinolone = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione
Methasone-type (16-methylated)
- Alclometasone = 7α-chloro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Beclometasone = 9α-chloro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
- Betamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
- Clobetasol = 9α-fluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dione
- Clobetasone = 9α-fluoro-16β-methyl-17α-hydroxy-21-chloropregna-1,4-diene-3,11,20-trione
- Clocortolone = 6α-fluoro-9α-chloro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Desoximetasone = 9α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Dexamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Diflorasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
- Difluocortolone = 6α,9α-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Fluclorolone = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dione
- Flumetasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Fluocortin = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20,21-trione
- Fluocortolone = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Fluprednidene = 9α-fluoro-11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
- Fluticasone = 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione
- Fluticasone furoate = 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione 17α-(2-furoate)
- Halometasone = 2-chloro-6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Meprednisone = 16β-methyl-17α,21-dihydroxypregna-1,4-diene-3,11,20-trione
- Mometasone = 9α,21-dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Mometasone furoate = 9α,21-dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 17α-(2-furoate)
- Paramethasone = 6α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
- Prednylidene = 11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
- Rimexolone = 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione
- Ulobetasol (halobetasol) = 6α,9α-difluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dione
- Amcinonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with cyclopentanone, 21-acetate
- Budesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with butyraldehyde
- Ciclesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with (R)-cyclohexanecarboxaldehyde, 21-isobutyrate
- Deflazacort = 11β,21-dihydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 21-acetate
- Desonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
- Formocortal (fluoroformylone) = 3-(2-chloroethoxy)-9α-fluoro-11β,16α,17α,21-tetrahydroxy-20-oxopregna-3,5-diene-6-carboxaldehyde cyclic 16α,17α-acetal with acetone, 21-acetate
- Fluclorolone acetonide (flucloronide) = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dione cyclic 16α,17α-acetal with acetone
- Fludroxycortide (flurandrenolone, flurandrenolide) = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetone
- Flunisolide = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
- Fluocinolone acetonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
- Fluocinonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone, 21-acetate
- Halcinonide = 9α-fluoro-11β,16α,17α-trihydroxy-21-chloropregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetone
- Triamcinolone acetonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
Others
- Cortivazol = 6,16α-dimethyl-11β,17α,21-trihydroxy-2'-phenyl[3,2-c]pyrazolopregna-4,6-dien-20-one 21-acetate
- RU-28362 = 6-methyl-11β,17β-dihydroxy-17α-(1-propynyl)androsta-1,4,6-trien-3-one
See also
References
- ↑ "Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia Lead to Transactivation of the Glucocorticoid Receptor". Endocrinology 156 (10): 3504–10. 2015. doi:10.1210/en.2015-1087. PMID 26207344.
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